1: triethylamine / heptane / 12 h / Heating 2: 81 percent / LiAlH4 / diethyl ether / 3 h / 20 °C 3: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 2 h; 2) 20 deg C, 12 h 4: 1) Li2CuCl4; 2) p-toluenesulfonic acid / 1) THF, 0 deg C, 3 h, then 20 deg C, 12 h; 2) methanol, water, 60 deg C, 3 h 5: 30 percent / C6H5SH / 2 h / 100 °C View Scheme

1: 1.) H2/Ni, 2.) LiAlH4 / 2.) ether 2: 7.5 g / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

lithium aluminium tetrahydride; hydrogen; nickel 2.) ether; Multistep reaction;

1: 1.) H2/Ni, 2.) LiAlH4 / 2.) ether 2: 7.5 g / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature 3: 1.) potassium tert-butanolate / 1.) DMF, 20 deg C, 3h, 2.) 5h View Scheme

1: 1.) H2/Ni, 2.) LiAlH4 / 2.) ether 2: 7.5 g / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature 3: 1.) potassium tert-butanolate / 1.) DMF, 20 deg C, 3h, 2.) 5h View Scheme

1: 69 percent / n-butyllithium / tetrahydrofuran / -78 °C 2: 49 percent / PhCH=Ru(PCy3)2Cl2 / CH2Cl2 / 12 h / Heating 3: 93 percent / H2 / 10 percent Pd on C / methanol / 18 h / 50 °C / 3800 Torr View Scheme

1: triethylamine / heptane / 12 h / Heating 2: 81 percent / LiAlH4 / diethyl ether / 3 h / 20 °C View Scheme

1: 1.) H2/Ni, 2.) LiAlH4 / 2.) ether 2: 7.5 g / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature 3: 1.) potassium tert-butanolate / 1.) DMF, 20 deg C, 3h, 2.) 5h 4: LiAlH4 / diethyl ether / 3 h / Heating 5: pyridine / 10 h / Ambient temperature View Scheme